Difficult Conversations: A Path to Growth and Connection.

Why is it so hard to say what needs to be said?

As we approach the holiday season, a time of joy, relaxation, and togetherness, many of us carry a persistent thought: “I should have had that conversation.” Perhaps it’s a conversation with your boss about your career, with your partner about unresolved tension, or with a friend about a lingering misunderstanding. The festive season might seem like a chance to escape such concerns, but these thoughts often linger, casting a shadow over the celebrations. Difficult conversations those discussions we procrastinate about are like a small rock in your shoe. Ignored, the rock becomes more painful with time. Yet, rather than removing it, we engage in what psychologists term "experiential avoidance." We tell ourselves, “It’s not the right time,” and delay the conversation. While this avoidance provides temporary relief, the unresolved issue resurfaces, taking up mental and emotional space.

In my experience as a global leadership coach, I’ve seen people carry unresolved conversations for years. Whether it’s about work, relationships, or personal boundaries, these lingering topics can lead to stress, hinder personal growth, and strain connections. However, addressing these conversations challenging as it may be offers immense relief, growth, and respect for yourself and others.

Similarly, in my practice as an executive coach, I often encounter leaders grappling with the fear of stepping outside their comfort zones. Whether it’s the fear of making bold decisions, addressing conflicts, or advocating for themselves, these moments of hesitation can limit both personal growth and organizational impact. Helping leaders overcome these fears and engage in transformative conversations is central to unlocking their potential, enabling them to lead with confidence, clarity, and courage.

By tackling both unresolved conversations and deeply ingrained fears, individuals and leaders alike can experience significant breakthroughs building stronger relationships, fostering resilience, and achieving meaningful progress in their personal and professional lives.

Why do we avoid these discussions? Several emotions and fears come into play:

Fear of rejection: We worry that addressing a sensitive topic might lead to rejection or conflict.

Shame: We may feel ashamed about the issue at hand or about bringing it up.

Fear of judgment: We’re concerned about what others will think of us.

Uncertainty: We don’t know how the other person will react, making us hesitant.

One striking example involved a client who was deeply afraid of asking for a pay raise, despite being highly qualified and delivering exceptional results. She felt that initiating the conversation might come across as pushy or even jeopardize her professional relationships. Her hesitation stemmed from fears of rejection and judgment, along with uncertainty about how her request would be received. During our coaching sessions, we explored the underlying beliefs fueling her fear and reframed her perspective. Together, we focused on the value she brought to her organization and the importance of aligning her contributions with fair compensation. Equipped with a structured approach and practice conversations, she successfully negotiated a significant raise. More importantly, she walked away with renewed self-confidence and an enhanced sense of self-worth.

Another client, a senior executive, hesitated to make decisions without exhaustive data, fearing that a wrong move could invite criticism or failure. This often led to analysis paralysis, delaying progress within his team. His fear of judgment and rejection by peers and stakeholders made it difficult to act decisively. Through coaching, we worked on embracing a mindset that balanced thorough analysis with timely decision-making. By developing a framework to assess risks and align decisions with strategic priorities, he grew more comfortable trusting his judgment. His newfound decisiveness not only boosted his effectiveness but also inspired his team to act with greater confidence.

These examples highlight that fear, while natural, is a surmountable obstacle. Whether it’s advocating for oneself, making difficult decisions, or navigating interpersonal dynamics, overcoming fear leads to profound growth. As a coach, my role is to guide leaders toward clarity, helping them rewrite the stories that hold them back and empowering them to step into their full potential.

We all experience these emotions that can make conversations challenging, creating a mental battlefield where avoidance feels like the safest option. However, the longer we delay, the more issues fester, leading to resentment, miscommunication, and missed opportunities. These difficult conversations often hold the key to growth, healing, and transformation. Though initiating them may feel uncomfortable, the rewards far outweigh the temporary discomfort.

Carrying unresolved issues is akin to lugging around a heavy emotional backpack. The stress, worry, and tension take up valuable mental and emotional space, holding us back. Addressing these issues lifts that weight, offering a profound sense of relief. A difficult conversation provides a chance to release pent-up feelings and let go of lingering concerns, creating a cathartic moment that paves the way for peace of mind. Challenging as they are, every difficult conversation presents an opportunity for growth. Confronting tough situations head-on builds resilience, strengthens our ability to handle future challenges, and boosts confidence. By stepping outside our comfort zones, we tap into the space where true personal growth happens.

Honesty, a cornerstone of trust, strengthens relationships. Opening up and sharing our perspectives demonstrates respect for the other person and the relationship itself. Vulnerability fosters deeper connections, showing a willingness to work through issues rather than avoiding them. Even when the discussion is hard, the shared experience can create a stronger bond. Uncertainty often feels more unsettling than an uncomfortable truth.

Difficult conversations bring clarity about emotions, situations, or the path forward. While outcomes might not always align with our hopes, knowing where we stand offers closure and the ability to move forward with purpose and direction, unclouded by assumptions or unanswered questions.

In facing these conversations, we unlock not just resolution but also transformation, strengthening our relationships and ourselves in the process.

It’s tempting to put off difficult conversations, hoping the issue will resolve itself or simply fade away. But avoidance often prolongs discomfort and creates new problems. Taking that first step might be uncomfortable, but the rewards emotional relief, personal growth, strengthened relationships, and clarity make it well worth the effort. Remember, courage isn’t the absence of fear; it’s taking action despite it. By initiating these conversations, you’re choosing growth, honesty, and connection over comfort, and that choice can lead to remarkable outcomes.

As an executive coach, I’ve seen firsthand the hesitation leaders experience when faced with tough conversations. Whether it’s discussing pay, addressing underperformance, or resolving conflicts, these moments can feel fraught with emotion and risk. Yet, despite the discomfort, initiating these conversations offers powerful rewards:

Emotional Relief: Addressing unresolved issues clears the mental and emotional weight of worry and stress. One client of mine described feeling as if “a stone had been lifted off their chest” after finally discussing a long-avoided topic with their board.

Personal Growth: Facing difficult situations builds resilience and confidence. A leader I coached found that addressing his fear of asking for a raise didn’t just lead to better compensation—it fundamentally changed how he viewed his ability to advocate for himself in all areas of life.

Strengthened Relationships: Honest conversations deepen trust. A senior executive I worked with repaired a strained partnership with a colleague by addressing unmet expectations directly, showing respect for the relationship through candor.

Clarity: Even if the outcome isn’t ideal, difficult conversations can provide a clear path forward. A leader who asked her boss about her future in the organization didn’t hear what she wanted but gained the clarity to pursue a new, fulfilling role elsewhere.

I often remind my clients: it’s easy to say, "just do it," but the actual process can feel daunting. Here are practical strategies from my experience that I’ve seen work in my coaching practice, supported by real-life examples:

1. Choose the right timing; Timing is critical. Addressing a sensitive issue in the heat of the moment can backfire. For instance, a client once tried to tackle their team’s underperformance right before a major deadline—it led to defensiveness and resistance. However, waiting for a calmer moment allowed for a more constructive and solution-oriented dialogue.

2. Be brief and direct; Overexplaining can dilute your message. One client needed to confront a teammate about missed commitments. Initially, their explanation was lengthy and convoluted, which risked confusing the issue. By refining their message to something concise like, “Your missed deadlines are affecting the team. Let’s discuss how we can address this,” they created clarity and set the stage for meaningful action.

3. Focus on the message; Fear of offending can lead to ineffective communication. A business leader I coached once softened their critique of a partner so much that the feedback wasn’t taken seriously. When they delivered the feedback respectfully but directly, the partner was able to take meaningful corrective steps. Similarly, a CEO addressing their partner’s missed deadlines revitalized the partnership by proposing accountability measures, leading to better communication and team performance.

4. Prepare for emotional reactions; Tough conversations can evoke strong emotions. For example, a client discussing pay equity with their boss anticipated defensiveness. By staying calm and composed, they were able to steer the conversation toward constructive solutions, even when the initial reaction was resistant. Another client avoided asking for a pay raise due to fear of rejection. Through preparation and role-play, they confidently outlined their value and career aspirations. While the raise didn’t come immediately, they gained clarity on the next steps and improved their relationship with their manager.

5. Use “I” statements; Blaming language can escalate tensions. A leader I worked with was frustrated with a disengaged team member and initially wanted to say, “You’re always late to meetings.” We shifted their approach to “I feel frustrated when meetings start late.” This change fostered a more collaborative atmosphere, enabling both parties to work toward a solution.

6. Practice active listening; Difficult conversations should be a two-way street. One client addressing a conflict with a peer learned that listening to the other’s perspective not only resolved the immediate issue but also strengthened their working relationship. In another example, a leader who had avoided discussing frustrations with a sibling for years found that active listening during their first conversation led to mutual understanding and a stronger bond.

7. End on a constructive note; Always leave room for solutions. After a tough performance discussion, one client concluded by asking, “How can I support you in meeting these expectations?” This shifted the tone from critique to collaboration, creating a path forward.

Closing Thoughts

Difficult conversations are just that difficult. Yet, they are essential for personal growth, healthier relationships, and emotional well-being. As we enter the holiday season, consider whether there’s a conversation you’ve been avoiding. By addressing it, you’re not only giving yourself the gift of relief and growth but also showing respect and care for the other person.

So, what’s the conversation you’ve been putting off? There’s no better time than now to start. Remember: every difficult conversation you face is an opportunity to grow and to give both yourself and others the respect they deserve.

About the Author Frans Hoek is the Managing Partner and CEO of Hoek Consultants, a global leadership consultancy. With extensive international and multicultural experience spanning diverse regions and industries, Frans specializes in assessing and developing leaders, driving high-impact change, and enhancing organizational performance. His expertise in leadership development strategies has made him a trusted mentor to senior executives and teams worldwide, helping them navigate the complexities of today's dynamic business environment. Frans emphasizes the critical importance of self-awareness, emotional intelligence, and personal growth as cornerstones of effective leadership, ensuring his clients are equipped to thrive in a globally connected world.

References

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2. Brown, B. (2012). Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead. Gotham Books.
3. Stone, D., Patton, B., & Heen, S. (2010). Difficult Conversations: How to Discuss What Matters Most. Penguin Books.
4. Hayes, S. C., Strosahl, K. D., & Wilson, K. G. (2016). Acceptance and Commitment Therapy: The Process and Practice of Mindful Change. Guilford Press.
5. Scott, S. (2004). Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time. Berkley Books.